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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:40 UTC
HMDB IDHMDB0000854
Secondary Accession Numbers
  • HMDB00854
Metabolite Identification
Common NameFormiminoglutamic acid
DescriptionFormiminoglutamic acid, also known as N-formimino-L-glutamate or formimino-glu, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Formiminoglutamic acid (FIGLU) is an intermediate in the metabolism of histidine. Formiminoglutamic acid is a very strong basic compound (based on its pKa). Formiminoglutamic acid exists in all living organisms, ranging from bacteria to humans. Within humans, formiminoglutamic acid participates in a number of enzymatic reactions. In particular, formiminoglutamic acid can be biosynthesized from 4-imidazolone-5-propionic acid; which is mediated by the enzyme probable imidazolonepropionase. In addition, tetrahydrofolic acid and formiminoglutamic acid can be converted into 5-formiminotetrahydrofolic acid and L-glutamic acid; which is catalyzed by the enzyme formimidoyltransferase-cyclodeaminase. In humans, formiminoglutamic acid is involved in histidine metabolism.
Structure
Data?1582752160
Synonyms
ValueSource
N-Formimidoyl-L-glutamateChEBI
N-Formimino-L-glutamateChEBI
N-Formimidoyl-L-glutamic acidGenerator
N-Formimino-L-glutamic acidGenerator
FormiminoglutamateGenerator
Formimino-gluHMDB
Formimino-L-glutamateHMDB
Formimino-L-glutamic acidHMDB
N-(Iminomethyl)-L-glutamic acidHMDB
N-Formimidoyl-glutamic acidHMDB
N-Formimino-glutamateHMDB
Acid, formiminoglutamicHMDB
FIGLUHMDB
Chemical FormulaC6H10N2O4
Average Molecular Weight174.1546
Monoisotopic Molecular Weight174.064056818
IUPAC Name(2S)-2-methanimidamidopentanedioic acid
Traditional NameN-formimino-L-glutamate
CAS Registry Number816-90-0
SMILES
OC(=O)CC[C@H](NC=N)C(O)=O
InChI Identifier
InChI=1S/C6H10N2O4/c7-3-8-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H2,7,8)(H,9,10)(H,11,12)/t4-/m0/s1
InChI KeyNRXIKWMTVXPVEF-BYPYZUCNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Formamidine
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.28 g/LALOGPS
logP-1.3ALOGPS
logP-2.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)10.88ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area110.48 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity48.71 m³·mol⁻¹ChemAxon
Polarizability15.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9400000000-6cceb3db80c1c51b5798Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fg9-9230000000-65123e05e539b5af2388Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0900000000-92c0f47c419298fb78a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-5900000000-8b915dd10756167a4003Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0012-9100000000-313b0983e834934e5682Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-1900000000-b264a846efb94105ac49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f97-5900000000-2f4ec838a8ef46f9428dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9200000000-a518077a6ec2f6a6c6c5Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified13.400-21.800 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.47 (0.0-0.80) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.90 +/- 0.71 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified780.114-1876.796 umol/mmol creatinineChildren (1-13 years old)BothGlutamate formiminotransferase deficiency details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Glutamate formiminotransferase deficiency
  1. Perry TL, Applegarth DA, Evans ME, Hansen S, Jellum E: Metabolic studies of a family with massive formiminoglutamic aciduria. Pediatr Res. 1975 Mar;9(3):117-22. [PubMed:235753 ]
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 229100 (Glutamate formiminotransferase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022280
KNApSAcK IDNot Available
Chemspider ID388370
KEGG Compound IDC00439
BioCyc IDN-FORMIMINO-L-GLUTAMATE
BiGG ID34986
Wikipedia LinkFormiminoglutamic acid
METLIN ID5817
PubChem Compound439233
PDB IDNot Available
ChEBI ID7274
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceTabor, Herbert; Rabinowitz, Jesse C. Insts. Formiminoglycine, formimino-L-aspartic acid, and formimino-L-glutamic acid.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Perry TL, Applegarth DA, Evans ME, Hansen S, Jellum E: Metabolic studies of a family with massive formiminoglutamic aciduria. Pediatr Res. 1975 Mar;9(3):117-22. [PubMed:235753 ]
  2. Hilton JF, Christensen KE, Watkins D, Raby BA, Renaud Y, de la Luna S, Estivill X, MacKenzie RE, Hudson TJ, Rosenblatt DS: The molecular basis of glutamate formiminotransferase deficiency. Hum Mutat. 2003 Jul;22(1):67-73. [PubMed:12815595 ]
  3. Haurani FI, Hall CA, Rubin R: Megaloblastic anemia as a result of an abnormal transcobalamin II (Cardeza). J Clin Invest. 1979 Nov;64(5):1253-9. [PubMed:500809 ]
  4. Verhoeven NM, Wanders RJ, Poll-The BT, Saudubray JM, Jakobs C: The metabolism of phytanic acid and pristanic acid in man: a review. J Inherit Metab Dis. 1998 Oct;21(7):697-728. [PubMed:9819701 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Folate-dependent enzyme, that displays both transferase and deaminase activity. Serves to channel one-carbon units from formiminoglutamate to the folate pool. Binds and promotes bundling of vimentin filaments originating from the Golgi (By similarity).
Gene Name:
FTCD
Uniprot ID:
O95954
Molecular weight:
58925.93
Reactions
5-Formiminotetrahydrofolic acid + L-Glutamic acid → Tetrahydrofolic acid + Formiminoglutamic aciddetails
5-Formiminotetrahydrofolic acid + L-Glutamic acid → Tetrahydrofolic acid + Formiminoglutamic aciddetails
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in cyclic amides
Specific function:
Not Available
Gene Name:
AMDHD1
Uniprot ID:
Q96NU7
Molecular weight:
46742.505
Reactions
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic acid + Hydrogen Iondetails
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic aciddetails